Methanol → 4-Methyl-pyridin 3-(4-methyl-thieno[3,2-c]pyridin-2-yl)-imidazolidin-2-one

HRID 80260

反応式

HRID 80260 の反応式
[C:1](=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:13]2[CH:14]=[C:15]([N:17]3[CH2:21][CH2:20][N:19]([C:22]4[CH:23]=[N:24][CH:25]=[CH:26][C:27]=4[CH3:28])[C:18]3=[O:29])[S:16][C:12]=2[CH:11]=[CH:10][N:9]=1.CB(O)O.CO>C(Cl)(Cl)Cl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:28][C:27]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1.[CH3:1][C:8]1[C:13]2[CH:14]=[C:15]([N:17]3[CH2:21][CH2:20][NH:19][C:18]3=[O:29])[S:16][C:12]=2[CH:11]=[CH:10][N:9]=1

参加物

7

反応物 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 498718701-(4-Chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

生成物 1

HCID 866494024-Methyl-pyridin 3-(4-methyl-thieno[3,2-c]pyridin-2-yl)-imidazolidin-2-one収率 16.39%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6212Chloroform溶媒

実験手順

Tetrakis (triphenylphosphine) palladium (33 mg, 0.0288 mmol) was added to potassium carbonate (120 mg, 0.8649 mmol) previously purged with argon (30 minutes). The reaction mixture was purged with argon for 15 minutes, followed by the addition of 1-(4-chloro-thieno[3,2-c]pyridin-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (98A: 100 mg, 0.2883 mmol) and methyl boronic acid (21 mg, 0.3459 mmol). The reaction mixture was heated to reflux for 6 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was concentrated to afford the crude product. Purification by column chromatography on silica gel (3-4% MeOH in CHCl3), followed by preparative HPLC afforded 10 mg of the product (16.39% yield).

後処理

  1. custompreviously purged with argon (30 minutes)
  2. customThe reaction mixture was purged with argon for 15 minutes
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 6 hours
  5. concentrationThe reaction mixture was concentrated
  6. customto afford the crude product
  7. customPurification by column chromatography on silica gel (3-4% MeOH in CHCl3)

出典と根拠

ORDレコード
ord-3712b84dc51a459bada732b0799aa2ca
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

読み込み中…